(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

Base Information

Chemical Name:(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate
CAS No.:1417795-97-1
Molecular Formula:C₆₁H₇₆O₈Si₂
Molecular Weight:993.441
Hs Code.:

(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

Synonyms:(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

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Chemical Property of (2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

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Technology Process of (2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

There total 26 articles about (2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

: 1417796-04-3
(S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid

: 1417796-06-5
(5R,6R)-6-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-5,6-dihydro-5-hydroxypyran-2-one

: 1417795-97-1
(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

Guidance literature:: (S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 1h;

(5R,6R)-6-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-5,6-dihydro-5-hydroxypyran-2-one; With dmap; In toluene; at 20 ℃; for 5h;
DOI:10.1016/j.tet.2012.11.051

Reference yield:

: 138499-16-8
2-[(tert-butyldiphenylsilyl)oxy]ethanol

: 1417795-97-1
(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 2 h / -20 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 12 h / Reflux

3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

4.1: lipase AK from Pseudomonas fluorescens / di-isopropyl ether / 20 °C / Molecular sieve; Inert atmosphere; Enzymatic reaction

5.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C

6.1: potassium carbonate; methanol / 20 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

7.2: -78 - 20 °C

8.1: dichloromethane / 24.5 h / 0 - 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C

10.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

10.2: 0 - 20 °C

11.1: lithium hydroxide; water / tetrahydrofuran / 48 h / 20 °C

12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C

12.2: 5 h / 20 °C

With 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; lipase AK from Pseudomonas fluorescens; 2,4,6-trichlorobenzoyl chloride; water; iodine; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether; toluene; mineral oil; 7.1: |Swern Oxidation / 8.1: |Wittig Olefination / 10.1: |Horner-Wadsworth-Emmons Olefination - Still-Gennari Modification / 12.1: |Yamaguchi Lactonization / 12.2: |Yamaguchi Lactonization;
DOI:10.1016/j.tet.2012.11.051

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1417795-97-1
(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 1H-imidazole; dmap / tetrahydrofuran / 24 h / 0 - 20 °C

2.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 2 h / -20 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

3.2: 12 h / Reflux

4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

5.1: lipase AK from Pseudomonas fluorescens / di-isopropyl ether / 20 °C / Molecular sieve; Inert atmosphere; Enzymatic reaction

6.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C

7.1: potassium carbonate; methanol / 20 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

8.2: -78 - 20 °C

9.1: dichloromethane / 24.5 h / 0 - 20 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C

11.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

11.2: 0 - 20 °C

12.1: lithium hydroxide; water / tetrahydrofuran / 48 h / 20 °C

13.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C

13.2: 5 h / 20 °C

With 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; lipase AK from Pseudomonas fluorescens; 2,4,6-trichlorobenzoyl chloride; water; iodine; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether; toluene; mineral oil; 8.1: |Swern Oxidation / 9.1: |Wittig Olefination / 11.1: |Horner-Wadsworth-Emmons Olefination - Still-Gennari Modification / 13.1: |Yamaguchi Lactonization / 13.2: |Yamaguchi Lactonization;
DOI:10.1016/j.tet.2012.11.051